One of the big issues in the practice of law these days is “e-discovery.” Since “discovery” is the process by which one party to a lawsuit tries to get useful information from another, you can probably guess that “e-discovery” involves digging through the other side’s electronically stored information or trying to keep them from digging through yours.

As Peter Henning (a former SEC lawyer) said recently, investigators searching through such information are especially interested in “any turn of phrase that can give them insight into what people were thinking” when they did the allegedly illegal, tortious, and/or stupid thing in question. E-mail searches can be especially valuable, he continued, “because e-mails are real-time and often unfiltered and can help to establish intent.” That is certainly true.

Because of the power of search engines, it pays to think creatively about what search terms might lead to interesting results. This applies both to potential diggers, whose searches will then be more effective, and to potential diggees, who should try to anticipate today what people may be searching for tomorrow.

This is yet another way in which we can learn from the bad example set by Lehman Brothers.

At least three lawsuits (so far) against Lehman and its former executives have made some use of search results obtained by bankruptcy examiner Anton Valukas, whose report on the circumstances of Lehman’s collapse was over 2,200 pages long. He and dozens of other lawyers searched through 34 million pages of internal Lehman documents, including 4.4 million emails, reportedly after brainstorming which search terms would be most useful. Because their searches seem to have been very productive, it is worth considering them in connection with your own e-mail practices. Perhaps you should print these out and post them where they will be most visible when your mouse pointer is hovering over the “send” button.

Here are a few of the actual search terms the examiner’s team used:

“risk”

“concern”

“let’s discuss”

“just between us”

“breach”

“big trouble”

“too late”

“stupid”

Personally, I’m not sure “let’s discuss” would be a very fruitful search term, but “big trouble” and “just between us” would definitely be on my list. In fact, I think starting any sentence with “just between us” is almost guaranteed to ensure that what you are about to say will not stay confidential, in the same way that it is usually a bad idea to precede any complex physical action with “Watch this!” or “I will now demonstrate.”

There were other phrases I noticed in some of the e-mails themselves that may or may not have been part of the team’s search terms, but which definitely are more examples of phrases to think very carefully about:

“bad company”

“perception issue”

“the real objectives”

“panicky,” “nervous,” or “anxious” (or any similar term)

“very slippery slope”

“true disaster”

“I’m trying to get out of [insert whatever you are into]”

“we have a desperate situation”

“I need another two billion”

“punished”

“stupidity”

“probably going to get punished for our stupidity”

If the team did not search for those, it should have. I think I would probably add most of those to any list of e-discovery searches, no matter what the case is about. That last one especially could be a real gold mine.

Additionally, although to my knowledge none of the following phrases surfaced in the Lehman emails, they occur to me as further terms to be carefully avoided:

“Ponzi” (or any other person after whom a type of scheme has been named)

“Madoff”

“Rothstein”

“Vlad the Impaler”

“British Petroleum”

“the red balloon flies at midnight”

“double down” (or any gambling term, really)

“plea bargain”

“no extradition treaty”

“Moldavian banking laws”

“secret hollow volcano base”

“now fulfill your destiny and take your father’s place at my side”

“we’re [insert expletive here]”

Finally, should something unfortunate turn up in one of your emails, as a last resort you might try the “just kidding” defense. A version of this was one of the top three suggestions recently offered by Jeff Skilling, the former CEO of Enron (there are a few more terms to avoid right there), to aspiring white-collar criminals who would prefer to avoid his mistakes and therefore imprisonment: (1) plead the Fifth, (2) go on a public-relations offensive, and (3) “don’t be sarcastic.” (I assume he was limited to three, and that “be honest” would have been next on the list.)

For example, Skilling said he was “being sarcastic” when he said to a group of people at Enron, “they’re on to us.” The court interpreted that as an admission of guilt, but according to Skilling it was just the opposite. Only one who was truly innocent would sarcastically admit his guilt, you see. (Seems to me this defense would apply in a wide variety of situations.) Of course, “[s]arcasm is easily misinterpreted,” Skilling admitted, “and can be a tremendous liability.”

Let’s just replace “sarcasm” with “e-mail,” and leave it at that. It really would be safer.